


Stiles' First Time

by KattsEyeDemon



Category: Teen Wolf (TV)
Genre: First Time, M/M, Porn, Stiles Stilinski Has a Big Dick, also Derek wants it, for, i love that that is a tag, really that's it, so much porn, sse17, stereksummerexchange17
Language: English
Status: Completed
Published: 2017-06-11
Updated: 2017-06-11
Packaged: 2018-11-12 17:52:31
Rating: Mature
Warnings: No Archive Warnings Apply
Chapters: 1
Words: 2,106
Publisher: archiveofourown.org
Story URL: https://archiveofourown.org/works/11166999
Author URL: https://archiveofourown.org/users/KattsEyeDemon/pseuds/KattsEyeDemon
Summary: Stiles' first time didn't go quite like he thought it would, especially once Derek saw him naked.Gift for "Addictedtobritishmen" On tumblr for the Sterek Summer Exchange 2017





	Stiles' First Time

**Author's Note:**

> As in the summary, this is for the Summer Exchange for the Sterek fandom 2017 <3 This was gifted to Addictedtobritishmen on Tumblr! Basically 2k+ of porn!

 

"...and I haven't done this before, obviously, I mean, I've talked about it a lot, I think everyone knows that - "

"I want it."

Stiles paused at the sound of Derek's voice, the boxers in his hand dropping to the floor. "...what?"

“I want it.”   Derek's eyes were dark and hungry, caught on the sight of Stiles' huge cock. “Fuck, I want it. You’ll do fine, I know you will, but I REALLY need you to fuck me.”

Stiles almost fell forward, raising an eyebrow. “Really?” he asked, unable to hide his skepticism. “I mean, of course, but it’s not like I’ve done this before, as I said, so I really need you to be sure-”

Derek’s eyes were locked on Stiles’, drifting down his body once again to settle on the huge cock between the newly minted 18 year old’s legs. “Yes.” he breathed, voice almost a growl.

“O-okay then. No pressure.” Stiles squeaked as Derek started stalking forward, tugging his henley over his head.

“You’ll do fine.” Derek murmured, pulling Stiles against him. “We’ll start with what we’ve already done, and let it progress from there, okay?”

Stiles nodded, pressing his face to Derek’s chest for a moment, taking a deep breath. “Deal. “he murmured, pulling back just a bit to kiss Derek, arms slipping around his neck.

 

They quickly moved to the bed, Derek tipping them both back and catching the flailing limbs as Stiles let out a small cry. He grinned, flashing his eyes again before he dove back into the kiss, tangling his hand in Stiles’ hair.

Stiles was straddling Derek’s thighs as he lifted up to breath, panting heavily as his hips rocked down. “Fuck. You have to be sure.”   
  
“Fuck yes I’m sure.” Derek growled playfully, hands on Stiles’ hips and digging in. 

Stiles groaned, reaching for his side table where the lube was, absently throwing a small thank you to the heavens that his dad was on a double shift. He was clumsy, struggling to open the lube and fumbling with the tube a bit before he finally managed, shifting to where he was between Derek’s legs. His hands shook as he slid one along the back of Derek’s thighs.

“C’mon, Stiles.” Derek coaxed. 

“Just...let me know if I hurt you, okay?” Stiles frowned in concentration, focus making his eyes lock onto Derek as he slowly slid a finger in, cursing under his breath.

Derek groaned appreciatively. “I will,” he promised. “But I won’t have to.”

Stiles tucked his hand under one knee, raising Derek’s leg just a bit. “You...you really want this?”

“There is nothing in the world that I want  _ more _ right now than for you to fuck me,” Derek insisted breathlessly, clenching down on Stiles’ finger. “Fuck.”

Stiles could only let out a breathy laugh. “Oh god.” He couldn’t believe it. “Are you ready for another?” he asked, crooking his finger a bit, trying to remember what he saw in porn and what he tried on himself.

Derek shook his head. “Bit more,” he panted. He  _ could _ take a second finger right now, but with how thick Stiles’ cock was, better to be thorough. 

Stiles couldn’t help the tiny grin that was stretching his face, eyes locked onto Derek. “God, you’re gorgeous. “He  breathed, slightly twisting and rocking his finger in and out.

“So are you,” Derek replied, thrusting his hips back against Stiles’ finger. “Need you to fuck me, fuck, please.”

“Can’t yet.” He said, leaning forward to kiss along Derek’s jaw. “Don’t want to hurt you.”

“So stretch me out,” Derek begged huskily. “Until I can take that fat cock of yours, god, I want it so bad.”

“Jesus Christ, Der.” Stiles groaned, squeezing his eyes shut as he focused on his breathing .”you want me to come before I’m even in you?” he slowly started working in another finger, making sure to take it almost glacial in pace.

Derek mewled, clenching down greedily on Stiles’ fingers.

“Damn,” Stiles groaned again, carefully twisting his fingers. “How in the hell am I going to be able to fit?”

“I can take it,” Derek promised hoarsely. “ _ Please _ .”

 

“You really want it, hmm?” His voice was more teasing than asking, his mouth running away from him. “What’s so special about me?”

“So fucking  _ thick _ ,” Derek breathed, his eyes dark. “Want it in me, want it stretching me out, so full, please Stiles.”

Stiles sucked in a breath. “Oh,” he couldn’t help but whisper, leaning down to whisper in Derek’s ear, fingers slowly scissoring. “You like this, huh? The fact that I have a big cock? Is that what has you basically a puddle on my bed?”

Derek squirmed as he nodded, moaning needily.

“God, that’s so fucking hot, sourwolf.” He sped his fingers up, mouthing at Derek’s ear. “You look like you’re starving for it.”

“Yeah?” Derek panted, grinning a little. “You want me begging?”

“Fuck yes. But at the same time, no. Like holy shit, I won’t make it if you do.” Stiles rambled, slipping a third finger into Derek when the other wasn’t paying attention to what Stiles’ HAND was doing.

Derek groaned at the stretch, eyes closing in pleasure. “I’ll wait for you to get it back up,” he promised. “I’d wait a week for your fucking cock.”

“You’re lucky I’m eighteen and have a wonderful recovery time.” Stiles said as he twisted his fingers, wanting to turn Derek into a babbling mess. “Because at the rate we’re going, I’m going to be doing good to slide in balls deep before coming. And then what’ll you do?”

“Beg you to stay,” Derek panted frankly. “Fuck, Stiles, just...fill me up,  _ please _ .”

“You think you’re ready for it?” Stiles panted, biting at and sucking up a mark on Derek’s neck that he knew would fade in seconds.

“I - I want…” Derek stuttered, groaning at the bite. “But...another finger first.”

Stiles didn’t say anything, just added another finger as his teeth found Derek’s skin once again.

“Ah - ah - oh,  _ fuck _ ,” Derek panted, stretching out his neck to expose it better to Stiles’ teeth. “Fuck me,” he begged, thrusting his hips back onto Stiles’ fingers.

“You ready?” he asked, voice low and shaky. “I need you to be sure.”

Derek looked up at Stiles, his eyes dark, but clear. “I won’t let you hurt me,” he said lowly. “Fuck me, Stiles, please.”

Stiles groaned, “Okay, how do you want me? Other than fucking you open, anyway.”

Derek couldn’t help but moan at that description. “I’m - it’ll be easier, if you fuck me from behind,” he admitted hoarsely.

“Easier? Or what you want to feel? The lack of control? I do watch porn, you know.” Stiles couldn’t help the teasing, carefully pulling his fingers free before licking his lips and turning to fumble around for a condom.

“Fuck, both,” Derek panted, shakily getting up onto his hands and knees.

Stiles managed to rip the wrapper open with his teeth before sliding it on, groaning quietly to himself as he gave himself a quick tug, eyes on Derek’s ass. “Ready?” He teased once again, free hand going to Derek’s hip.

 

Derek shivered in anticipation, thinking  _ I was ready hours ago _ . “Go slow, at first,” he warned. “Just in case.”

“ ‘course.” Stiles murmured, guiding himself to Derek’s hole before slowly starting to push in, his hands clinging to Derek’s hips with a sharp noise as he sank.

Derek let out a high-pitched, needy noise as Stiles’ cock started to stretch him out. God, it was so good.

“Fuckfuckfuck.” Stiles cursed, trembling as he managed to bottom out. “Just. Shh, don’t move. Please.” He groaned. “Please, just...FUCK.”

Derek froze, wanting so much to clench down, to feel even more how big Stiles’ cock was inside him, stretching him out so perfectly.

“Sorry.” Stiles panted. “Just… Fuck, I’m so close.” he groaned, shifting a bit to rest his head on Derek’s back, breathing slowly and carefully as he focused on pulling himself back from the edge.

Derek swallowed hard, trembling, aware of every place that Stiles’ skin touched his, and even  _ more _ aware of Stiles’ cock, shifting ever so slightly inside him. “Take your time,” he said roughly. “I...fuck, Stiles, I’d wait for you forever.”

“Sap.” Stiles panted, voice fond as he carefully sat back up, a hand running up Derek’s back to his tattoo, covering it with one spread hand as the free hand clenched at Derek’s hip. “Gonna fuck you now. Ready?”

“ _ Fuck _ yes,” Derek panted, his head dropping forward. “Please.”

Stiles started slow, moving and shifting, unable to keep his hips from grinding in small circles as he tried to figure out the best way to go about it.  God this was more intense than any porn he’d seen.

Derek mewled, overwhelmed. “So much,” he panted. “Please.”

“I’ve got you. “He murmured, his own voice shaky as he pushed down just a bit on Derek’s back, starting to slowly rock in and out, nails of his hands curling into Derek’s skin. “Jesus you’re so fucking tight.”

“ ‘s cause you’re so fucking  _ big _ ,” Derek countered, breathing hard. “Fuck, never stop.”

“Like it?” He teased, voice breathy as he rocked forward just a bit harder, setting a harder pace.

“God, yes,” Derek panted. 

Stiles took his time, slowly upping the pace little by little, the speed bit by bit, until he was all but slamming into Derek, almost all rhythm gone.

Breathless, wordless, all Derek could think about was Stiles’ cock stretching him out, filling him up, overwhelming him.

“Fuck, So fucking hot.” Stiles groaned, hand slipping around Derek’s waist to brush along his cock. He didn’t want to be the first one to go, the cliche’d fast finisher. Yup, had nothing to do with his fantasy of Derek coming on his cock, nothing at all.

Derek cried out, clenching down.

“Sh-shit.” Stiles groaned, curling his hand around Derek’s cock. “C’mon, Der.” he panted. “Come for me. Come on my cock.”

“Little more,” Derek begged breathlessly. “Fuck it out of me, Stiles, wish I could feel it for days.”

Stiles groaned. “Fuck, you’re going to make ME come that way. “He sat up until he could grab both of Derek’s hips, almost yanking him back onto Stiles’ cock, punching out small groans and grunts out of his chest.

“Oh, fuck,” Derek panted, reaching under himself to stroke his cock hard and fast. “Fuck, Stiles, god, so good, so - ah - need you so bad.”

Stiles curled his fingers tightly, knowing that anyone else would be carrying the bruises for days only making him hold on tighter, thrust harder. “So fucking tight. So hot. How the hell….”

Derek squeezed down, clenching rhythmically around Stiles’ cock. “I’m close,” he warned. “Fill me up, Stiles,  _ please _ .”

“Shit!” he cried out, slamming into Derek as he came, the clenching and the begging sending him over the edge head first.

Derek moaned in satisfaction as he felt Stiles’ cock pulse inside him. It was only a few moments before he followed Stiles over the edge.

“Jesus Christ on a cracker.” Stiles panted, leaning over to kiss at Derek’s tattoo as he followed Derek down until they were both laying on the bed, him on Derek still.

Slowly, Derek caught his breath, a satisfied smile spreading across his face as he hummed his agreement.

Stiles nuzzled into Derek’s skin, moving slowly and carefully as he pulled free, tieing and tossing the condom somewhere in the area of his trashcan before flopping to the side of Derek. “I love you.” he breathed.

“Love you too,” Derek agreed softly. He cuddled into Stiles, his smile turning into a grin. “Love your cock, too.”

Stiles let out a startled laugh. “Oh my god!” he grinned brightly, tugging Derek closer. “How in the hell did I get so lucky? A lovely sap, hot as fuck, AND a dork? I won the lottery!”

“Same to you,” Derek said smugly, tucking his face into Stiles’ neck.

Stiles just laughed softly, cuddling Derek close and hugging him tight. “I fucked you loopy.” He mused, kissing Derek’s temple. “I’ll have to keep that trick in mind.”

Derek nipped affectionately at Stiles’ throat, nuzzling against him. “ ‘zat mean you’ll fuck me more?” he asked.

Stiles tilted his head back, a small smile still on his face. “Yeah, that means I’ll fuck you more. But don’t hog all of it, kay? Tradesies are a thing that will exist, dammit.”

Derek laughed a little. “Fair,” he agreed.

“Hmmm, gimme five minutes, we’ll start that deal then.” Stiles smiled, though he made no move to even twitch from where he was curled half around Derek.

 

 

 

 

 

 

 

 

 

 

 


End file.
